Acetone → HCID 178440097, compound

Reaction equation

[BH4-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:16][CH2:17][CH3:18])[NH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:5])[CH3:4].CC(C)=O>C(O)C>[OH:5][CH:3]([C:6]1[N:7]=[C:8]([CH2:16][CH2:17][CH3:18])[NH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:4]

Participants

Procedure

125 mg of sodium borohydride were added to a solution of 1.50 g of ethyl 4-acetyl-2-propylimidazole-5-carboxylate [prepared as described in step (ii) above] in 15 ml of ethanol, and the resulting mixture was stirred at room temperature for 30 minutes. 2 ml of acetone were added, and the mixture was stirred for a further 10 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, and the concentrate was dissolved in methanol. The solution was again concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using 1:20 and 1:10 by volume mixtures of methylene chloride and methanol as the eluent, to give 1.32 g of the title compound as crystals, melting at 151°-153° C.